Methanol → N-((1-(6-((2,6-Diisopropylphenylamino)methyl)pyridin-2-yl)naphthalen-2-yl)methyl)-2,4,6-trimethylaniline

HRID 2370669Notes

Reaction equation

HRID 2370669 reaction equation
CO.[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:7]=1[N:15]=[CH:16][C:17]1[N:22]=[C:21]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][C:24]=2[CH2:33][NH:34][C:35]2[C:40]([CH3:41])=[CH:39][C:38]([CH3:42])=[CH:37][C:36]=2[CH3:43])[CH:20]=[CH:19][CH:18]=1)([CH3:5])[CH3:4].[BH3-]C#N.[Na+].[BH4-]>C(O)=O.C1(C)C=CC=CC=1>[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:7]=1[NH:15][CH2:16][C:17]1[N:22]=[C:21]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][C:24]=2[CH2:33][NH:34][C:35]2[C:36]([CH3:43])=[CH:37][C:38]([CH3:42])=[CH:39][C:40]=2[CH3:41])[CH:20]=[CH:19][CH:18]=1)([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 28123BorohydrideHCID 5003444Sodium cyanoborohydrideHCID 68003896N-((1-(6-((2,6-Diisopropylphenylimino)methyl)pyridin-2-yl)naphthalen-2-yl)methyl)-2,4,6-trimethylaniline

Product 1

HCID 68003915N-((1-(6-((2,6-Diisopropylphenylamino)methyl)pyridin-2-yl)naphthalen-2-yl)methyl)-2,4,6-trimethylaniline

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 1140TolueneSolvent

Procedure

Methanol (30 mL), toluene (10 mL), and compound 6b (2.11 g, 3.91 mmol) were heated to reflux under nitrogen. Formic acid (95%) (5 drops) was added followed by portions of NaBH3CN (0.983 g, 15.6 mmoL). The borohydride was added in four portions over an hour. After 3 hours at reflux the yellow color of the imine had faded completely and the volatiles were removed by evaporation on a rotary evaporator. Water (20 mL) and Et2O (30 mL) were added, and the organics were separated and dried over brine. The ether solution was then dried over MgSO4, filtered, and evaporated to give the diamine 7o as a pale pink solid. Yield: 2.1 g, 99%. 1H NMR (500 MHz, CD2-Cl2): 7.90 (t, 2H), 7.82 (t, 1H), 7.56 (d, 1H), 7.38-7.52 (m, 4H), 7.29 (d, 1H), 7.07 (d, 2H), 7.03 (m, 1H), 6.74 (s, 2H), 4.28 (m, 2H), 4.08 (br t, 1H), 3.96 (br, 2H), 3.45 (m, 1H), 3.33 sept, 2H), 2.19 (s, 3H), 2.05 (s, 6H), 1.15 (d, 12H).

Workup

  1. temperatureto reflux under nitrogen
  2. customthe volatiles were removed by evaporation on a rotary evaporator
  3. additionWater (20 mL) and Et2O (30 mL) were added
  4. customthe organics were separated
  5. dry with materialdried over brine
  6. dry with materialThe ether solution was then dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4a85c47e807a4b8a9886622d63887603
Source dataset
uspto-grants-2014_04
Patent number
US08710163B2

Reaction notes

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